Tryptamine → HCID 21940715, compound

HRID 1243074Notes

Reaction equation

HRID 1243074 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.I[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].CN[C@@H]1CCCC[C@H]1NC>[Cu]I.CO.C(Cl)Cl.C1(C)C=CC=CC=1>[C:14]1([N:6]2[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:4]([CH2:3][CH2:2][NH2:1])=[CH:5]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

9

Reactant 4

HCID 1150TryptamineHCID 11575IodobenzeneHCID 62657Potassium Phosphate, TribasicHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamine

Product 1

HCID 21940715HCID 21940715, compoundYield 87.2%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 887MethanolSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

Using the general procedure, tryptamine (0.160 g, 1.00 mmol) was coupled with iodobenzene (134 μL, 1.20 mmol) using CuI (9.5 mg, 0.050 mmol, 5.0 mol %), K3PO4 (2.1 mmol), trans-N,N′-dimethyl-1,2-cyclohexanediamine (32 μL, 0.20 mmol, 20 mol %) and toluene (1.0 mL) to give the crude product. Column chromatography (2×15 cm, methylene chloride (saturated with ammonia):methanol 50:1) provided 0.206 g (87% yield) of the product as a yellow oil. 1H NMR (400 MHz, CDCl3): δ 7.65 (m, 1H), 7.55 (m, 1H), 7.47 (m, 4H), 7.31 (m, 1H), 7.18 (m, 3H), 3.06 (t, J=7 Hz, 2H), 2.94 (t, J=7 Hz, 2H), 1.40 (bs, 2H).

Workup

  1. customto give the crude product

Sources & evidence

ORD record
ord-9cfe64c2ec904940871ada1c20845697
Source dataset
uspto-grants-2006_10
Patent number
US07115784B2

Reaction notes

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